I was on a call when someone asked a straightforward question that had a binary answer (yes or no). The person responded with a five minute explanation with a lot of details, all factually correct and contextually relevant, but at the end still didn’t answer the question.

My partner in my first company (Dave Jilk – now the CEO of Standing Cloud) used to have an endearing way of dealing with this. Here’s how it would play out.

Dave: “Is the release going to be on time?”

Software Engineer Dave was Talking To: “Blah blah blah, five minute explanation of all the things that he was struggling with, why everything was difficult, what the risks were on timing, blah blah blah, why the client was giving mixed signals and changing things, and can’t I have a faster computer please?”

Dave: “That was a yes or no question.”

We spend a lot of time getting derailed in our work. I’m as guilty of it as anyone as I often answer a question with a story from my experience. Sometimes that’s a helpful thing to do; other times I should just answer “yes” or “no.”

The corollary to this is to ask why. I’m a huge fan of the 5 Whys approach and went through it with a long time friend and CEO of a company I have an angel investment in at dinner last night. He’s been struggling with some stuff and I explained how (and why) he should be using 5 Whys to try to get to the root cause of the issue, rather than staying on the surface and not actually learning anything. In his case he was experiencing the opposite of the yes/no problem – he was trying to ask an open ended question and getting a yes/no answer. For example:

CEO Friend: “Are the trials converting into customers?”

CTO: “No”

The appropriate response from my CEO Friend in this case would have been “Why?” And I’d predict he’d need to ask “why?” several (four?) more times before he got enough information to actually know what was going on.

I encourage all CEO’s in the world to use these two approaches judiciously. Don’t ask me why – just do it.